


Then Again, Privacy is Overrated

by sakuranomi808



Category: Supernatural
Genre: Did I mention Underage, M/M, Masturbation, Sam is really young in this, Sex Toys, Weecest
Language: English
Status: Completed
Published: 2020-12-24
Updated: 2020-12-24
Packaged: 2021-03-10 22:54:17
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,773
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28274907
Author URL: https://archiveofourown.org/users/sakuranomi808/pseuds/sakuranomi808
Summary: Written for SPN Kink Meme Prompt: Dean/toy Sam/toy Dean/Sam, masturbation, comeKinks-Dean/pocket pussy, Sam/pocket pussy, Dean/Sam, masturbation, dry orgasm, come play12 year old Sam walks in on Dean fuck a cheap pocket pussy/ cocksleeve. Sam knows about sex and jerking off but he’s shocked and aroused to see Dean fucking into a sextoy like that. So he just stands there watching until dean laughs and tells him to get a closer look if he wants.He ends up on the bed right next to Dean, tucked into his arm, watching as Dean’s cock thrusts in and out of the toy. Dean teases him about how hard he is and has Sam pull down his shorts. Dean comes looking at Sam’s little cock. Sam watches as Dean comes inside the toy, as Dean slides it off his wet cock, and as Dean slides the wet toy onto Sam’s cock. Sam can feel how wet and warm it is from Dean’s come as Dean pumps it up and down. Dean gets off on watching Sam’s boy cock slide through his come and his come drip down onto Sam that he beats off with the other hand until he comes onto Sam’s tummy while watching Sam shake through a dry orgasm
Relationships: Dean Winchester/Sam Winchester
Comments: 8
Kudos: 253





	Then Again, Privacy is Overrated

Growing up like they did, privacy was really a foreign concept -- like something that other, normal kids who grew up in the suburbs in two-story houses with picket-fences had, but not them. 

What they had was this: Sam pulled open the motel room door and was immediately greeted by the filthy sight of his big brother laid out half-naked on the bed, fucking into some kind of fleshy rubber thing. 

“Close the door, would you,” Dean said absently. 

“Jesus fuck, Dean,” Sam said, slamming the door shut behind him. He let his backpack slide off his shoulder and onto the floor, but his feet felt frozen in place. 

“If you ask me what I’m doing, then clearly we need a do-over on the good ol’ sex talk,” Dean said, finally raising his eyes to meet Sam’s. He didn’t stop what he was doing though, just kept on sliding that thing up and down his dick with one hand and tweaking and pinching his nipple with the other. 

“I- I know what you’re doing,” Sam stammered. “I just didn’t… I haven’t…” 

“You mean, you use your hand to jerk off?” Dean scoffed, more statement than question. “Amateur,” he added, a mischievous glint in his eyes. 

Sam’s mouth was bone dry, and he knew he was gaping like a moron, but he couldn’t seem to look away. Sure, he’d seen his brother naked before, but never like this. Dean was wearing only his jeans and they were undone, the open flaps of them revealing the waist of his briefs tucked down under his balls, making them look obscenely swollen and huge. His cock was obviously rock-solid, the veins criss-crossed along the shaft throbbing as Dean worked the toy over his erection again and again. 

“C’mon,” Dean said, a little breathless as he gestured for Sam to come closer. “You can get a better look if you want.” 

Sam’s brain was misfiring in every direction. Obviously, he should turn around and leave, give Dean some privacy to finish what he was doing. And he ought to be disgusted as well that he had even seen his brother masturbating; but instead, he found himself closing the distance between them and kicking off his shoes, sliding onto the bed beside his big brother. He instinctively leaned in closer when Dean curled an arm around his shoulder, pulling him close like he had so many times before. 

“Where’d you get it from?” Sam licked his lips, watching intently as Dean stopped and pulled the toy off. It made a filthy-hot sucking noise against his skin when he did it, and Sam swallowed something between a moan and a gasp at the sound of it. 

“That shady looking place next to the gas station,” Dean replied as he grabbed a bottle of lube from the nightstand. "It's called a pocket pussy. Cause... well, you know," he added as he presented it to Sam to inspect. It sort of did look like a pussy, or at least what Sam imagined one would look like.

Dean flicked open the bottle and drizzled some of the clear liquid onto his cock-head, then smoothed it down over his shaft. Sam unconsciously leaned in, amazed by how incredibly hard Dean was; how arousing and surprisingly intimate it was looking this closely at his brother’s engorged dick. Dean was big -- a lot longer and thicker than Sam was, anyway -- his stiff shaft curved just a bit where the tip was straining up toward his navel. It was all shiny and wet with lube, but there was also a clear glob of pre-come beading at the slit, just starting to drip down the big, mushroom-shaped crown. 

“Dean, you’re so hard,” Sam breathed, unable to keep his voice steady as he finally tore his gaze away from his brother’s cock and looked up into his eyes. He felt like a total idiot stating the obvious like that, but Dean just chuckled and brought his hand up to ruffle Sam’s hair as he slid the toy onto his dick and started pumping again. 

“Looks like you’re pretty hard there yourself, kiddo,” Dean teased as he nodded pointedly at Sam’s shorts obviously tenting up. 

“I’m not as big as you,” Sam frowned, heat coloring his cheeks as he tried to squirm away. But Dean gently squeezed his shoulders, wordlessly keeping him there. 

“Can I see?” Dean asked quietly. “It’s only fair,” he added with a little grin. “Gonna have to start charging you for these shows otherwise. C’mon, Sammy. It’s just me. Don’t be embarrassed.” 

Sam sighed and lifted up enough to shove at the waist of his shorts and briefs. The truth was that he wanted Dean to see, wanted Dean to touch, to take what had always been his anyway. He hiked up his t-shirt under his armpits and kicked his briefs down and off, finally dropping his gaze down to look at his own dick. He was definitely hard, and immensely grateful for that, since his arousal at least gave him a couple more inches on top of his meager length. 

Awkwardly curling his hand around his own shaft, Sam looked up at his brother again for guidance. He had just figured out not very long ago how nice it felt to touch himself there; had woken up a few times with his dick hard and throbbing and couldn’t resist stroking himself under the covers in the darkness while Dean slept just a few feet away. He wasn't even sure if he'd truly come before, though. It always felt really good, but he was too afraid to keep going. That was as far as it had ever gone, and he was hopelessly unsure of what to do next. 

Sam wasn’t prepared for the moan that escaped his brother’s lips. His eyes darted up to Dean’s face and then back down to his cock where he’d picked up the pace a bit, still working the pussy up and down, over and over again. Sam couldn’t decide what was hotter -- Dean’s cheeks flushing pink and his freckles growing more pronounced with his arousal, or his dick making a dirty-wrong squelching sound every time it disappeared into the rubber hole. 

“Sammy, that’s so hot,” Dean choked out. He caught his lip between his teeth, biting down hard as he started to buck his hips up, meeting his downstrokes halfway as he fucked into the pussy. Sam watched in wide-eyed awe as Dean’s thrusts grew erratic and he came with a groan, his movements stilling momentarily as he pushed impossibly deeper into the toy and unloaded into it. 

Sam’s own breaths had grown ragged without him realizing it. He was aroused beyond belief, but found himself unable to move or even comprehend what was happening when Dean carefully pulled the toy up and off of his own softening cock and reached over to slide it down onto Sam’s dick. Sam’s brain violently misfired again, a barrage of sensations tearing through him, his body and mind screaming at him -- wet, warm, tight, Dean -- all at once. 

“Oh- oh, God,” Sam managed to choke out. Almost against his will, he began to thrust his hips up, chasing after more of that wonderfully tight, wet heat. 

“Feel good?” Dean asked. “Got it nice and wet for you, Sammy. Look at my come, it's all over you now." 

Sam forced his eyes open and gasped at the sight of his brother’s release, all pearly-white and sticky, dripping out of the pussy to wet Sam’s hard shaft. Dean wasn’t letting up, either, was still pumping the toy rhythmically over Sam’s cock again and again, more of his come leaking down onto Sam’s dick and balls with every thrust. 

“Dean,” Sam groaned. “It feels so good. Please- please,” he murmured, unsure exactly what he was begging for. 

“Sam,” Dean breathed. “Fuck. I- I need-” 

Sam frowned a bit, wondering why Dean had stopped until he realized that he was shifting over and switching hands, now using one to continue pumping the pussy over Sam’s cock and the other to start jerking himself off again. 

“Got me so hot, Sammy,” Dean groaned, his voice gravel-rough, sounding like pure sin. “So hard for you again. You gonna come for me, little brother?” 

The endearment is ultimately what pushed Sam over the edge and he cried out sharply, his whole body shuddering as his orgasm tore violently through him. The pleasure was insane, like nothing he'd ever felt before, washing over him in jagged waves. He was still riding them out when he felt Dean’s movements stutter and pause for a moment. Sam looked down and sucked in a gasp as Dean leaned in closer and abruptly shot his load all over Sam’s chest and stomach, his come feeling almost burning-hot as it spurted out in streaks against Sam’s flushed, sweaty skin. Dean continued to pump his own hard dick until there was nothing left, then gently trailed the spongy-soft head of it over Sam's navel where his come had started to pool. 

Sam hissed softly when Dean carefully pulled the toy away from his softening, sensitive flesh and set it down on the nightstand. It was quiet now between them -- maybe a little too quiet -- but Sam couldn’t quite find the words as he watched his brother absently thumb through the mess of cooling come on Sam’s belly. 

"It's not wrong, or bad," Dean said, licking his lips as he reached over to grab some tissues to start cleaning them both up. "It's a completely natural thing to do. You know that, right?" 

Sam just shrugged and shook his head, not sure what Dean was expecting him to say. His body was still thrumming pleasantly and he hadn't felt this relaxed in a long time, but the fact still remained that he had just jerked off -- had his first real orgasm -- with his big brother's help, and that couldn't possibly be right. 

"Think of it as… practice," Dean continued on. "Figuring out what feels good before you do it for real." 

"Yeah," Sam finally agreed. It had certainly felt real to him just a few moments ago. It didn't totally make sense but if Dean was okay with it, then so was Sam. "Okay, yeah Dean. Thanks." 

"Any time," Dean grinned. "Just- ask me first if you wanna use it, all right? I get first dibs 'cause I'm older. And you can figure out how to wash this thing out." 

"Jerk," Sam muttered, even though he was smiling as Dean finished wiping up his stomach and tossed the wad of tissues into the trash can. 

"Bitch," Dean replied fondly.


End file.
